A new meroterpenoid from endophytic fungus Talaromyces amestolkiae CS-O-1

doi:10.1016/j.bse.2020.104186

Biochemical Systematics and Ecology

Volume 93, December 2020, 104186

https://doi.org/10.1016/j.bse.2020.104186 Get rights and content

Highlights

•
Seven compounds were isolated from the endophytic fungus Talaromyces amestolkiae CS-O-1.
•
Compound 1 is a new meroterpenoid compound.
•
Compounds 2–6 were isolated for the first time in Talaromyces genus.
•
The significance of chemotaxonomy for these compounds was discussed.

Abstract

Talaromyces amestolkiae CS-O-1, isolated from Tripterygium Wilfordii Hook. f., was identified based on its ITS and 18S rDNA gene sequencing. A new meroterpenoid, chrodrimanin T (1), along with six known compounds, nicotinamide (2), penipyridone D (3), penipyridone A (4), 3-benzylidene-8,8a-dihydroxy-2-methyl-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione (5), butyl-isobutyl-phthalate (6), and aspergillumarin A (7), were isolated from Talaromyces amestolkiae CS-O-1. The structures and relative configurations of these compounds were established by the analysis of HRMS, 1D and 2D-NMR spectroscopy and the comparison with data in the literature. The compounds 2–6 were first isolated from Talaromyces genus. Herein, the chemotaxonomic significance of these compounds is described.

Section snippets

Subject and source

Talaromyces, a genus of fungi which can be found in a wide range of sources including oceans (Dewapriya et al., 2018), soils (He et al., 2016), plants (Zhai et al., 2015) and even house ash (Visagie et al., 2014). Talaromyces belongs to the family Trichocomaceae. In 1955, Benjamin described Talaromyces as the sexual state of Penicillium. The species contain soft ascocarp fruiting bodies whose cell walls are composed of tightly interwoven hyphae (Benjamin, 1955).

The stain, CS-O-1, was isolated

Previous work

Previously, T. amestolkiae was mostly isolated from mangrove, and was never found in Tripterygium wilfordii Hook. f. So far, only two studies reported the chemical constituents of T. amestolkiae including terpenes, benzofurans and isocoumarins (Chen et al., 2016, 2018). In addition, there is no literature published on chemotaxonomic investigations of this species.

General experimental procedures

Semi-preparing HPLC was achieved on SEP 1530 LC series (Separation Technology Co., Ltd., Beijing) using semi-prep column (10 × 250 mm, 5 μm, park Pro C18, YMC, Tokyo, Japan). High-resolution ESI-MS were recorded on a waters QDA mass spectrometer (Waters Technology (Shanghai) Co., Ltd.). 1D and 2D-NMR spectra were tested on an Avance III 600 nuclear magnetic resonance spectrometer (Bruker, Switzerland). Silica gel (100–200 mesh and 200–300 mesh) was purchased from Qingdao Ocean Chemical Factory,

Chemotaxonomic significance

In this study, one meroterpenoid (1), four alkaloids (2-5), and two esters (6–7), were isolated from T. amestolkiae and their structures were identified. 1 is a new compound and compounds 2–6 are isolated from the genus Talaromyces for the first time.

As we known, a series of chrodrimanin meroterpenoids have been obtained from Talaromyces, which include chrodrimanins A-H isolated from Talaromyces sp. YO-2 (Hayashi et al., 2012a; Hayashi et al., 2012b). In addition, chrodrimanins I-J were

CRediT authorship contribution statement

Yunmei Fu: Writing - original draft, Investigation. Chunhe Li: Writing - original draft, Investigation. Jing Zhu: Formal analysis. Luting Zhang: Formal analysis. Yu Wang: Investigation. Qili Chen: Formal analysis. Liang Xu: Resources. Songya Zhang: Conceptualization, Methodology, Writing - review & editing, Supervision. Yue Fang: Conceptualization, Methodology, Writing - review & editing, Supervision. Tao Liu: Conceptualization, Methodology, Writing - review & editing, Supervision, Project

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgements

This study was funded by National Natural Science Foundation of China (81302672, 81703373) and Basic Scientific Research Project for Colleges and Universities from Department of Education of Liaoning Province (LFWK201721).

References (24)

S. Chen et al.
Phytochemistry
(2018)
S.C. Chen et al.
Mar. Drugs
(2019)
A. Hussain et al.
Bioorg. Med. Chem. Lett
(2017)
F.D. Kong et al.
Fitoterapia
(2017)
X.F. Li et al.
Nat. Prod. Res.
(2019)
C.M. Visagie et al.
Stud. Mycol.
(2014)
J. Bao et al.
Mar. Drugs
(2018)
C.R. Benjamin
Mycologia
(1955)
T. Bu et al.
Phytother Res.
(2010)
Y. Chen et al.
Magn. Reson. Chem.
(2009)

S.H. Chen et al.

RSC Adv.

(2016)

P. Dewapriya et al.

Front Chem

(2018)

Cited by (7)

Natural sesquiterpene quinone/quinols: chemistry, biological activity, and synthesis
2023, Natural Product Reports
Covering: 2010 to 2021
Sesquiterpene quinone/quinols (SQs) are characterized by a C15-sesquiterpenoid unit incorporating a C6-benzoquinone/quinol moiety. Numerous unprecedented carbon skeletons have been constructed with various connection patterns between the two parts. The potent anti-cancer, anti-inflammatory, anti-microbial, anti-viral, and fibrinolytic activities of SQs are associated with their diverse structures. The representative avarol has even entered the stage of clinical phase II research as an anti-HIV agent, and was developed as paramedic medicine against psoriasis. This review provides an overall summary of 558 new natural SQs discovered between 2010 and 2021, including seven groups and sixteen structure-type subgroups, which comprehensively recapitulates their chemical structures, spectral characteristics, source organisms, biological activities, synthesis, and biosynthesis, aiming to expand the application scope of this unique natural product resource.
Bioactive terpenoids derived from plant endophytic fungi: An updated review (2011–2020)
2022, Phytochemistry
Citation Excerpt :
Chrodrimanin T (443), a new meroterpenoid, was identified from endophytic Talaromyces amestolkiae CS-O-1, obtained from Tripterygium Wilfordii Hook. f., (Fu et al., 2020). Chemical investigation of Talaromyces purpureogenus yielded seven meroterpenoids, talaromyolides E-K (444–450).
Plant endophytes have been considered as novel sources of naturally occurring compounds with various biological activities, including cytotoxic, antimicrobial, anti-inflammatory, anticancer, herbicides, antileishmanial and antioxidant. A variety of specialised products, comprising terpenoids, alkaloids, polyketides, phenolic compounds, coumarins, and quinone derivatives have been reported from various strains. An increasing number of products, especially terpenoids, are being isolated from endophytes. Herein, the isolated new terpenoids from plant endophytic fungi, their hosts, as well as biological activities, from January 2011 until the end of 2020 are reviewed. In this period, 516 terpenoids are classified into monoterpenes (5), sesquiterpenes (299), diterpenes (76), sesterterpens (22), meroterpenes (83), triterpenes (29), and other terpenoids (2), were isolated from different plant endophytic fungi species.
Chemical constituents from marine derived fungus Talaromyces cellulolyticus SHJ-3 and its chemotaxonomic significance
2022, Biochemical Systematics and Ecology
Citation Excerpt :
To data, more than 20 analogues have been discovered from the Trichocomaceae family, including Penicillium sp., Talaromyces sp., and Talaromyces funiculosum (Hayashi et al., 2012; Zhou et al., 2015). Recently, studies reported two new chrodrimanins K-T, which were isolated from the marine worm derived fungus Penicillium sp. and the plant endophytic fungus Talaromyces amestolkiae, respectively (Kong et al., 2017a,b; Fu et al., 2020). Additionally, four novel derivatives, talaromyolides A−D, with novel 6/6/6/5/5/5 and 6/6/6/6/6/6 polycyclic skeletons were identified from the marine fungus Talaromyces sp.
Based on the MS/MS molecular networking target separation strategy, chemical investigation of the ethyl acetate extract of the marine coral derived fungus Talaromyces cellulolyticus SHJ-3 afforded a series of chrodrimanin meroterpenoids, namely, verruculide A (1), chrodrimanin A (2), chrodrimanin B (3), chrodrimanin C (4), chrodrimanin F (5), chrodrimanin H (6), along with two phenolic structures, 6-hydroxymellein (7) and N-(4-hydroxy-2-methoxyphenyl) acetamide (8). Their chemical structures were elucidated via NMR spectroscopic analysis, HRESIMS experiment, single-crystal X-ray diffraction, and compared with those reported in the literature. Among them, compound 7 was isolated from the genus of Talaromyces for the first time. Additionally, the chemotaxonomic significance of these compounds was also discussed. Overall, this work will enrich the chemical diversity and provide useful information for chemotaxonomic study on the genus of Talaromyces.
Natural products from the Picea foliar endophytes Niesslia endophytica sp. nov. and Strasseria geniculata
2023, Mycological Progress
Fungal Biodiversity of Potato Tubers
2023, Mikologiya I Fitopatologiya
New Meroterpenoid and Isocoumarins from the Fungus Talaromyces amestolkiae MST1-15 Collected from Coal Area
2022, Molecules

View all citing articles on Scopus

¹: The two authors contributed equally to this work.

View full text

A new meroterpenoid from endophytic fungus Talaromyces amestolkiae CS-O-1

Highlights

Abstract

Section snippets

Subject and source

Previous work

General experimental procedures

Chemotaxonomic significance

CRediT authorship contribution statement

Declaration of competing interest

Acknowledgements

Phytochemistry

Mar. Drugs

Bioorg. Med. Chem. Lett

Fitoterapia

Nat. Prod. Res.

Stud. Mycol.

Mar. Drugs

Mycologia

Phytother Res.

Magn. Reson. Chem.

RSC Adv.

Front Chem